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Many islands have minimum stay requirements before you can get married. For instances, it's 3 days in the BVI's and 2 days for Anguilla. You can research all the legal requirements for marriage on any island here: www.islandbrides.com

i'd make st. john your "home" island. US - so easy to get marriage arranged - think you have to stop at the courthouse on st. thomas to do paperwork. has all you want except beachfront unless you stay at the westin. caneel would be nice but out of your price range. most people rent villas - many of which have gorgeous views & pools & tradewinds to keep you cool.
lots of stunning spots for your wedding. have not used but know there are some good & helpful wedding planners on st. john